And the Sporting News provides us with an excellent opportunity to go all Fire Joe Morgan on them.
Starting late in the 2012 season, Cherington pulled off a series of moves that helped that turned a last-place team into the 2013 World Series champs:
A last-place team that brought back a 4.4 WAR second baseman, a 2.9 WAR DH, a 1.9 WAR catcher, a 1.9 WAR third baseman, a 1.4 WAR center fielder, a 1.0 WAR left fielder, and three starting pitchers at 3.2, 1.9, and 1.5 WAR. In other words, eight out of fourteen primary positions were already filled by 1.5+ WAR players, with three of them in the 3+ WAR neighborhood.
In August 2012, Cherington dumped three of the team's biggest contracts — Josh Beckett, Adrian Gonzalez and Carl Crawford — in a trade with Los Angeles Dodgers, saving the Red Sox about $261.7 million.
All three signed their contracts while Cherington was a Red Sox Senior VP and Assistant GM (Beckett in April of 2010, Gonzalez in April of 2011, and Crawford in December of 2010). If only there had been some way he could have had some influence on their signing in the first place...
After the season, he fired controversial manager Bobby Valentine and hired Toronto Blue Jays manager John Farrell — a former Sox pitching coach — to replace him. Players credited Farrell with bringing calm to clubhouse after a year of the tumultuous Valentine.
Valentine, of course, was originally hired in November, 2011 by Red Sox General Manager... Ben Cherington.
Mike Napoli: $13M
Stephen Drew: $9.5M
Shane Victorino: $13M
Koji Uehara: $9.25M (2 years)
Those four mid-market players cost the Red Sox about $40M in 2013. He also signed replacement-level Ryan Dempster for 2/$26.5M. The Red Sox' total payroll was $150M.
The keys to winning Sporting News Executive of the Year? Saddle your team with overpaid veterans and a dysfunctional manager who you can dump a year later and replace by spending $55M on free agents to supplement your 20-WAR core.